family with young children enjoying time at a pool at their large vacation home

Relax by the pool with your family at Bear's Den Vacation Home

Vacation Home Rentals

Explore Kissimmee Vacation Rentals

Stay your way in the Vacation Home Capital of the World®

The ultimate home away from home is a Kissimmee vacation rental. The area offers more than 22,000 professionally managed properties, ranging from affordable, single-family homes to 15-bedroom mansions and luxury villas. With spacious floor plans, private pools, and just about every amenity under the sun, you can enjoy all the comforts of home and then some. Plus, world-famous theme parks are practically in your backyard.

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Vacation Home Capital of the World®

Kissimmee, Florida is the Vacation Home Capital of the World and with more than 30,000 homes to choose from, it’s no wonder where we got the name from.

Vacation homes are more than just your average accommodations. These properties are located in gated communities that have an array of unique amenities such as prestigious golf courses, incredible restaurants, extreme pools and water parks, and more. Not sure where to get started? Use this page as a guide to all your questions and we’ll help out along the way!

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A beautiful vacation home rental in Kissimmee
Jeeves Florida Rentals

Jeeves Florida Rentals

10 Reasons to Choose a Vacation Home Rental in Kissimmee

With more and more vacation home rentals being added each year, we've compiled 10 reasons why you should choose Kissimmee as your home away from home.

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vacation home, kissimmee
Practicing magic with a wand and a cauldron in a room full of candles

Photo: Encore Resort Homes

Surround Yourself with Magic in These Unique Vacation Homes!

With game rooms, bedrooms, and in-house theaters, these vacation home rentals make for a magical place to stay.

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Stay, Work & Play Together in Kissimmee

Pair work with play when you stay in Kissimmee. The Vacation Home Capital of the World® allows you to do it all: work, play, relax, and stay in style!

Stay & Save in a Kissimmee Vacation Home

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Find the perfect place to stay for your crew in Kissimmee.


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Snapshots of fun vacation home adventures in the heart of Florida!